86197-24-2Relevant academic research and scientific papers
Importance of allylic interactions and stereoelectronic effects in dictating the steric course of the reaction of iminium ions with nucleophiles. An efficient total synthesis of (±) gephyrotoxin
Overman,Lesuisse,Hashimoto
, p. 5373 - 5379 (2007/10/02)
A stereocontrolled total synthesis of (±)-gephyrotoxin in 15 steps and 6.5% overall yield from benzyl trans-1,3-butadiene-1-carbamate is described. A key step is reduction of octahydroquinoline 27 from the more hindered concave α face to provide decahydroquinoline 28. This unusual transformation results from the interplay of allylic (A1,2) steric interactions and stereoelectronic effects.
